Theo Epstein had highs and lows in Boston

Timeline: GM helped end 86-year championship drought

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In 2004, Theo Epstein (foreground) assembled a roster that became the Red Sox’ first World Series champions in 86 years.

October 12, 2011

Theo Epstein’s 9-year run as general manager of the Red Sox appears to be over, as team sources have confirmed he has accepted a job with the Chicago Cubs.

With two World Series championships and six playoff appearances under his belt, Epstein will go down as the most successful general manager in team history. But the Brookline native wasn’t perfect -- he also presided over several free agent busts, and leaves behind a team embroiled in controversy after a historic September collapse.

Here’s a look back at some of the memorable moments of the Epstein Era.

November 2002: Epstein, just 28, is named general manager of the Red Sox. He had previously served as assistant general manager after joining the organization in March 2002.

May 2003: Epstein made his first big trade with the acquisition of pitcher Byung-Hyun Kim from the Arizona Diamondbacks for infielder Shea Hillenbrand. Kim would eventually become the Red Sox’ closer and save 16 games that season, which began with the team attempting to close games by committee.

October 2003: The Red Sox were eliminated from the ALCS by the Yankees after a crushing Game 7 defeat in extra innings. The team then parted ways with manager Grady Little.

November 2003: Epstein acquired Curt Schilling from the Diamondbacks in a blockbuster deal. It came after he spent Thanksgiving at Schilling’s Arizona home attempting to convince the starter to waive his no-trade clause.

December 2003: The Red Sox hired Terry Francona as the second manager in Epstein’s tenure. Later in the month, Epstein signed former A’s closer Keith Foulke to a four-year contract. Epstein also aggressively pursued a trade for then-Rangers shortstop Alex Rodriguez, only to see the Yankees pull the trigger on a deal for the slugger two months later.

July 2004: Epstein gambled by trading disgruntled franchise icon Nomar Garciaparra at the trading deadline. A series of deals landed Garciaparra in Chicago and Orlando Cabrera, Dave Roberts and Doug Mientkiewicz in Boston. The Red Sox went on a 20-2 run shortly after the deals en route to the postseason.

October 2004: The roster Epstein assembled came back from a 3-0 series deficit to beat the Yankees in the ALCS and then swept the Cardinals in the World Series for the Red Sox’ first championship since 1918.

December 2004: The Red Sox allowed another franchise icon, Pedro Martinez, to leave via free agency and sign a long-term deal with the Mets (an Epstein decision that was validated when Martinez tore his rotator cuff less than two years later). Epstein also made one of his most glaring personnel mistakes when he signed Edgar Renteria to a four-year contract. A year later, the underachieving shortstop would be dealt to the Braves.

October 2005: The Red Sox were swept 3-0 by the White Sox in the ALDS. At the end of the month, Epstein announced he would not return to the Red Sox as general manager following a dispute with management. He left Fenway Park that night in a gorilla suit in an effort to evade reporters.

January 2006: Epstein returned as general manager after clearing up problems with Red Sox management. He had remained an unofficial advisor to the club in the interim. (The club acquired Josh Beckett and Mike Lowell during his absence.) “Looking back, before Oct. 31 obviously we were not all on the same page when it came to the vision of this organization,” Epstein told Sports Illustrated at the time. “That’s been resolved in the last 10 weeks. That shared vision goes a long way in creating a harmony throughout the front office. I believe that we were not going to get to that point without (his resignation) happening.”

October 2006: Red Sox missed the playoffs with a record of 86-76, the team’s worst record since 2001.

December 2006: Red Sox made international headlines by signing premier Japanese free-agent pitcher Daisuke Matsuzaka to a six-year contract. For the second time in two years, Epstein signed a free-agent shortstop that would come back to haunt him. Julio Lugo inked a four-year, $36 million deal, but would be dumped by the Red Sox in July 2009.

January 2007: The Red Sox signed free-agent outfielder J.D. Drew to a five-year, $70 million deal. Epstein also married his girlfriend, Marie Whitney.

July 2007: Epstein acquired closer Eric Gagne in a deadline-day deal with the Rangers. Gagne, who left as a free agent after the season, moved into a set-up role for the Red Sox but was not a factor down the stretch (2-2, 6.75 ERA).

October 2007: Red Sox won their second World Series in four years.

July 2008: Epstein finally parted ways with Manny Ramirez, the dynamic slugger whom the general manager had tried to move several times before. The Red Sox dealt him to the Dodgers in a trade that netted them Pirates outfielder Jason Bay.

October 2008: The Red Sox were eliminated in Game 7 of the ALCS by the Tampa Bay Rays. And while some of Epstein’s personnel moves were backfiring, others were flourishing. Dustin Pedroia, whom Epstein drafted in 2004, won AL MVP honors, one year after being named Rookie of the Year. And Matsuzaka went 18-3, which gave him a two-year record of 33-15.

October 2010: The Red Sox finished in third place in the AL East with a record of 89-73.

December 2010: Epstein acquired perhaps the two biggest-name players of his Red Sox tenure when he signed free agent Carl Crawford and traded for first baseman Adrian Gonzalez. Crawford agreed to a seven-year, $142 million deal, while Boston sent three top prospects to San Diego for Gonzalez.

January 2011: With third baseman Adrian Beltre signing in Texas and catcher Victor Martinez joining Detroit, the Red Sox allowed two of their three best offensive players from the 2010 season to leave as free agents.

June 2011: The Red Sox parted ways with Cameron, who hit seven home runs and had 24 RBIs in Boston after signing a two-year deal worth $15.5 million.

July 2011: Epstein acquired starting pitcher Erik Bedard from the Mariners at the trading deadline.

September 2011: The Red Sox set a major league record by blowing a 9-game playoff lead in September, when they won just seven of 27 games. After entering the season the World Series favorite among many analysts, they finished 90-72, one game out of playoff contention.

October 2011: About two weeks after Francona left the Red Sox after eight seasons as manager, Epstein reached an agreement with the Cubs to take a front-office role, according to sources.